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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1939
https://doi.org/10.1107/S1600536810025833

9,9-Bis[4-(prop-2-yn­yl­oxy)phen­yl]-9H-fluorene

Kiramat Shah,a Muhammad Raza Shaha and Seik Weng Ngb*

aH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 30 June 2010; accepted 1 July 2010; online 7 July 2010)

In the title compound, C31H22O2, the bond angle at the C atom belonging to the five-membered ring of the fluorene system is opened to 112.64 (12)°. The two benzene rings are twisted with respect to the fluorene ring system at dihedral angles of 72.81 (6) and 81.83 (6)°. One Car­yl—O—C—C≡ fragment is extended, with a C—O—C—C torsion angle of −178.77 (13)°, but the other Car­yl—O—C—C≡ fragment is bent, with a C—O—C—C torsion angle of 64.78 (19)°. Inter­molecular weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the synthesis of copolyethers having 1,3,4-oxadiazole rings and fluorene groups from the polymerization of 9,9-bis­(4-propargyloxyphen­yl)fluorene, see: Hamciuc et al. (2009[Hamciuc, C., Hamciuc, E., Ipate, A. M., Cristea, M. & Okrasa, L. (2009). J. Appl. Polym. Sci. 113, 383-391.]). For a related structure, see: Shah et al. (2010[Shah, K., Yousuf, S., Raza Shah, M. & Ng, S. W. (2010). Acta Cryst. E66, o1705.]).

[Scheme 1]

Experimental

Crystal data

  • C31H22O2

  • Mr = 426.49

  • Orthorhombic, P 21 21 21

  • a = 11.0047 (8) Å

  • b = 12.9686 (9) Å

  • c = 15.4371 (11) Å

  • V = 2203.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.35 × 0.25 × 0.15 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 21245 measured reflections

  • 2861 independent reflections

  • 2658 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.082

  • S = 1.04

  • 2861 reflections

  • 306 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.20 e Å−3

  • Absolute structure: 2204 Friedel pairs were merged

  • Flack parameter: ?

  • Rogers parameter: ?

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C29—H29A⋯O1i 0.99 2.46 3.358 (2) 151
Symmetry code: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810025833/xu2792sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025833/xu2792Isup2.hkl

checkCIF report


Comment top

9,9-Bis(4-propargyloxyphenyl)fluorene is the mononer required for the synthesis of other copolyethers (Hamciuc et al., 2009); these polymers typically possess good solubility in inorganic solvents, high thermal stability and high glass transition temperatures. The compound is readily synthesized from commercially available 9,9-bis(4-hydroxyphenyl)fluorene and propargyl bromide. A previous report detailed the structure of the product of its reaction with t-butyl bromoacetate (Shah et al., 2010). In the C31H22O2 molecule (Scheme I, Fig. 1), the angle at the carbon atom belonging to the five-membered fluorenyl ring that is connected to two p-phenylene rings is open to 116.1 (1) ° by the rings. One four-atom Caryl–O–C–C≡ fragment is coplanar with the ring [C—O–C–C torsion angle 1.2 (1) °] but the other is bent [torsion angle 64.8 (2) °].

Related literature top

For the synthesis of copolyethers having 1,3,4-oxadiazole rings and fluorene groups from the polymerization of 9,9-bis(4-propargyloxyphenyl)fluorene, see: Hamciuc et al. (2009). For a related structure, see: Shah et al. (2010).

Experimental top

9,9-Bis(4-hydroxyphenyl)fluorene (0.5 g, 1.4 mmol) was dissolved in acetone (25 ml) to give a clear solution. Potassium carbonate (0.7 g, 5 mmol) was added and the mixture stirred for an hour. Propargyl bromide (0.7 ml, 5 mmol) was added and stirring continued overnight. The mixture was filtered; prismatic crystals separated from the solution in 80% yield.

Refinement top

The acetylenic H-atoms were located in a difference Fourier map, and were refined with a distance restraint of C–H 0.95±0.01 Å; their temperature factors were refined. Other H atoms were placed in calculated positions [C–H 0.95–0.99 Å, U(H) = 1.2U(C)] and were included in the refinement in the riding model approximation. Friedel pairs were merged as no significant anomalous scattering.

Structure description top

9,9-Bis(4-propargyloxyphenyl)fluorene is the mononer required for the synthesis of other copolyethers (Hamciuc et al., 2009); these polymers typically possess good solubility in inorganic solvents, high thermal stability and high glass transition temperatures. The compound is readily synthesized from commercially available 9,9-bis(4-hydroxyphenyl)fluorene and propargyl bromide. A previous report detailed the structure of the product of its reaction with t-butyl bromoacetate (Shah et al., 2010). In the C31H22O2 molecule (Scheme I, Fig. 1), the angle at the carbon atom belonging to the five-membered fluorenyl ring that is connected to two p-phenylene rings is open to 116.1 (1) ° by the rings. One four-atom Caryl–O–C–C≡ fragment is coplanar with the ring [C—O–C–C torsion angle 1.2 (1) °] but the other is bent [torsion angle 64.8 (2) °].

For the synthesis of copolyethers having 1,3,4-oxadiazole rings and fluorene groups from the polymerization of 9,9-bis(4-propargyloxyphenyl)fluorene, see: Hamciuc et al. (2009). For a related structure, see: Shah et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C31H22O2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
9,9-Bis[4-(prop-2-ynyloxy)phenyl]-9H-fluorene top
Crystal data top
C31H22O2F(000) = 896
Mr = 426.49Dx = 1.286 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7024 reflections
a = 11.0047 (8) Åθ = 2.3–27.7°
b = 12.9686 (9) ŵ = 0.08 mm−1
c = 15.4371 (11) ÅT = 100 K
V = 2203.1 (3) Å3Block, colorless
Z = 40.35 × 0.25 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer		2658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
ω scansh = −14→14
21245 measured reflectionsk = −16→16
2861 independent reflectionsl = −19→20
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.3105P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2861 reflectionsΔρmax = 0.18 e Å−3
306 parametersΔρmin = −0.20 e Å−3
2 restraintsAbsolute structure: 2204 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods
Crystal data top
C31H22O2V = 2203.1 (3) Å3
Mr = 426.49Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.0047 (8) ŵ = 0.08 mm−1
b = 12.9686 (9) ÅT = 100 K
c = 15.4371 (11) Å0.35 × 0.25 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer		2658 reflections with I > 2σ(I)
21245 measured reflectionsRint = 0.042
2861 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0322 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å−3
2861 reflectionsΔρmin = −0.20 e Å−3
306 parametersAbsolute structure: 2204 Friedel pairs were merged
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.24715 (9)0.37529 (9)1.06380 (7)0.0184 (3)
O20.72277 (11)0.74489 (10)0.66169 (7)0.0228 (3)
C10.84334 (14)0.71897 (12)1.07308 (10)0.0146 (3)
C20.93879 (15)0.78830 (12)1.08005 (11)0.0174 (3)
H21.00720.78321.04280.021*
C30.93255 (15)0.86561 (13)1.14272 (11)0.0200 (3)
H30.99790.91301.14880.024*
C40.83115 (16)0.87398 (13)1.19668 (11)0.0205 (3)
H40.82780.92761.23850.025*
C50.73513 (16)0.80494 (13)1.18992 (11)0.0188 (3)
H50.66600.81111.22640.023*
C60.74238 (14)0.72624 (13)1.12841 (10)0.0156 (3)
C70.65875 (14)0.64169 (13)1.10835 (10)0.0169 (3)
C80.54672 (15)0.61615 (14)1.14465 (11)0.0206 (3)
H80.51280.65651.19000.025*
C90.48567 (15)0.52999 (15)1.11285 (12)0.0226 (4)
H90.40970.51091.13720.027*
C100.53482 (15)0.47162 (14)1.04579 (12)0.0211 (4)
H100.49220.41291.02510.025*
C110.64577 (15)0.49837 (13)1.00872 (11)0.0189 (3)
H110.67820.45930.96210.023*
C120.70800 (14)0.58268 (13)1.04078 (10)0.0157 (3)
C130.82912 (13)0.62794 (12)1.01042 (10)0.0143 (3)
C140.93668 (14)0.55407 (12)1.02154 (10)0.0145 (3)
C150.93030 (15)0.46837 (13)1.07548 (11)0.0167 (3)
H150.85530.45191.10270.020*
C161.03105 (14)0.40609 (13)1.09059 (10)0.0170 (3)
H161.02480.34771.12750.020*
C171.14088 (14)0.43008 (13)1.05113 (11)0.0151 (3)
C181.14950 (14)0.51457 (12)0.99593 (11)0.0160 (3)
H181.22430.53030.96820.019*
C191.04803 (14)0.57562 (12)0.98172 (10)0.0160 (3)
H191.05420.63340.94410.019*
C201.23372 (16)0.26883 (13)1.08654 (12)0.0210 (4)
H20A1.19070.23131.03990.025*
H20B1.18590.26231.14060.025*
C211.35523 (17)0.22575 (14)1.09882 (11)0.0222 (4)
C221.4531 (2)0.19125 (17)1.11001 (14)0.0342 (5)
C230.81257 (14)0.66357 (13)0.91600 (10)0.0153 (3)
C240.76842 (14)0.76168 (13)0.89833 (10)0.0163 (3)
H240.75880.80920.94470.020*
C250.73786 (15)0.79255 (13)0.81480 (11)0.0186 (3)
H250.70750.86000.80430.022*
C260.75237 (15)0.72339 (14)0.74710 (10)0.0182 (3)
C270.79946 (15)0.62612 (15)0.76239 (11)0.0210 (4)
H270.81190.57990.71550.025*
C280.82856 (15)0.59607 (13)0.84623 (11)0.0192 (3)
H280.85970.52880.85630.023*
C290.67080 (16)0.84363 (14)0.64399 (11)0.0221 (4)
H29A0.66280.85180.58050.027*
H29B0.72720.89770.66490.027*
C300.55120 (16)0.86010 (14)0.68398 (11)0.0203 (3)
C310.45729 (17)0.87683 (15)0.71807 (12)0.0254 (4)
H221.5337 (13)0.167 (2)1.1183 (19)0.073 (10)*
H310.3818 (13)0.8907 (17)0.7453 (13)0.036 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0141 (5)0.0153 (6)0.0257 (6)0.0011 (5)0.0006 (5)0.0027 (5)
O20.0289 (6)0.0249 (6)0.0146 (5)0.0056 (5)−0.0034 (5)0.0000 (5)
C10.0168 (7)0.0140 (7)0.0130 (7)0.0024 (6)−0.0032 (6)0.0020 (6)
C20.0182 (7)0.0176 (8)0.0164 (8)−0.0001 (6)−0.0016 (6)0.0003 (6)
C30.0233 (8)0.0157 (8)0.0209 (8)−0.0031 (7)−0.0052 (7)0.0008 (7)
C40.0292 (8)0.0168 (8)0.0154 (7)0.0034 (7)−0.0040 (7)−0.0016 (6)
C50.0212 (8)0.0205 (8)0.0147 (7)0.0045 (7)−0.0007 (6)0.0001 (7)
C60.0161 (7)0.0167 (8)0.0140 (7)0.0031 (6)−0.0021 (6)0.0020 (6)
C70.0165 (7)0.0184 (8)0.0159 (7)0.0021 (6)−0.0024 (6)0.0027 (6)
C80.0160 (7)0.0267 (9)0.0192 (8)0.0023 (7)−0.0003 (6)0.0019 (7)
C90.0140 (7)0.0283 (9)0.0256 (9)−0.0019 (7)0.0001 (7)0.0063 (8)
C100.0167 (7)0.0196 (8)0.0269 (9)−0.0035 (6)−0.0053 (7)0.0031 (7)
C110.0171 (7)0.0181 (8)0.0215 (8)0.0007 (6)−0.0025 (7)0.0006 (7)
C120.0145 (7)0.0161 (8)0.0164 (7)0.0017 (6)−0.0026 (6)0.0036 (6)
C130.0144 (7)0.0131 (7)0.0153 (7)0.0007 (6)−0.0004 (6)0.0003 (6)
C140.0146 (7)0.0151 (8)0.0138 (7)0.0007 (6)−0.0012 (6)−0.0017 (6)
C150.0154 (7)0.0188 (8)0.0158 (8)−0.0021 (6)0.0008 (6)0.0007 (6)
C160.0186 (7)0.0163 (8)0.0159 (8)−0.0001 (6)−0.0007 (6)0.0031 (6)
C170.0149 (7)0.0142 (8)0.0162 (7)0.0000 (6)−0.0018 (6)−0.0032 (6)
C180.0154 (7)0.0160 (8)0.0166 (8)−0.0025 (6)0.0014 (6)−0.0009 (6)
C190.0192 (7)0.0126 (7)0.0160 (8)−0.0018 (6)0.0005 (6)0.0012 (6)
C200.0219 (8)0.0149 (8)0.0263 (9)−0.0003 (7)−0.0036 (7)0.0033 (7)
C210.0292 (9)0.0181 (8)0.0195 (8)0.0046 (7)0.0028 (7)0.0010 (7)
C220.0337 (10)0.0411 (12)0.0279 (10)0.0200 (10)0.0063 (9)0.0081 (9)
C230.0137 (7)0.0172 (8)0.0151 (7)−0.0003 (6)−0.0010 (6)−0.0002 (6)
C240.0173 (7)0.0151 (8)0.0165 (7)0.0005 (6)−0.0011 (6)−0.0031 (6)
C250.0203 (8)0.0151 (8)0.0205 (8)0.0011 (7)−0.0041 (7)0.0005 (7)
C260.0172 (7)0.0227 (8)0.0149 (7)−0.0005 (6)−0.0009 (6)−0.0002 (7)
C270.0224 (8)0.0235 (9)0.0169 (8)0.0036 (7)−0.0017 (6)−0.0040 (7)
C280.0208 (8)0.0161 (8)0.0206 (8)0.0037 (6)−0.0023 (7)−0.0021 (7)
C290.0247 (8)0.0233 (9)0.0184 (8)0.0012 (7)−0.0012 (7)0.0044 (7)
C300.0265 (8)0.0175 (8)0.0170 (8)−0.0020 (7)−0.0052 (7)0.0025 (7)
C310.0265 (9)0.0253 (10)0.0243 (9)−0.0038 (8)0.0013 (7)−0.0011 (8)
Geometric parameters (Å, º) top
O1—C171.3824 (18)C14—C191.399 (2)
O1—C201.432 (2)C15—C161.391 (2)
O2—C261.387 (2)C15—H150.9500
O2—C291.429 (2)C16—C171.389 (2)
C1—C21.387 (2)C16—H160.9500
C1—C61.405 (2)C17—C181.391 (2)
C1—C131.534 (2)C18—C191.386 (2)
C2—C31.395 (2)C18—H180.9500
C2—H20.9500C19—H190.9500
C3—C41.397 (2)C20—C211.462 (2)
C3—H30.9500C20—H20A0.9900
C4—C51.389 (2)C20—H20B0.9900
C4—H40.9500C21—C221.179 (3)
C5—C61.396 (2)C22—H220.949 (10)
C5—H50.9500C23—C241.389 (2)
C6—C71.465 (2)C23—C281.399 (2)
C7—C81.394 (2)C24—C251.391 (2)
C7—C121.403 (2)C24—H240.9500
C8—C91.393 (3)C25—C261.386 (2)
C8—H80.9500C25—H250.9500
C9—C101.392 (3)C26—C271.384 (2)
C9—H90.9500C27—C281.389 (2)
C10—C111.392 (2)C27—H270.9500
C10—H100.9500C28—H280.9500
C11—C121.382 (2)C29—C301.469 (2)
C11—H110.9500C29—H29A0.9900
C12—C131.530 (2)C29—H29B0.9900
C13—C141.532 (2)C30—C311.180 (3)
C13—C231.540 (2)C31—H310.949 (10)
C14—C151.390 (2)
C17—O1—C20116.28 (12)C14—C15—H15119.2
C26—O2—C29117.13 (13)C16—C15—H15119.2
C2—C1—C6120.56 (15)C17—C16—C15119.34 (15)
C2—C1—C13128.68 (14)C17—C16—H16120.3
C6—C1—C13110.75 (13)C15—C16—H16120.3
C1—C2—C3118.85 (15)O1—C17—C16124.00 (14)
C1—C2—H2120.6O1—C17—C18115.70 (14)
C3—C2—H2120.6C16—C17—C18120.29 (15)
C2—C3—C4120.58 (16)C19—C18—C17119.46 (15)
C2—C3—H3119.7C19—C18—H18120.3
C4—C3—H3119.7C17—C18—H18120.3
C5—C4—C3120.86 (15)C18—C19—C14121.46 (15)
C5—C4—H4119.6C18—C19—H19119.3
C3—C4—H4119.6C14—C19—H19119.3
C4—C5—C6118.61 (15)O1—C20—C21107.81 (14)
C4—C5—H5120.7O1—C20—H20A110.1
C6—C5—H5120.7C21—C20—H20A110.1
C5—C6—C1120.52 (15)O1—C20—H20B110.1
C5—C6—C7130.92 (15)C21—C20—H20B110.1
C1—C6—C7108.56 (14)H20A—C20—H20B108.5
C8—C7—C12120.73 (16)C22—C21—C20179.0 (2)
C8—C7—C6130.43 (16)C21—C22—H22177 (2)
C12—C7—C6108.84 (14)C24—C23—C28117.77 (15)
C9—C8—C7118.38 (17)C24—C23—C13120.14 (14)
C9—C8—H8120.8C28—C23—C13121.74 (14)
C7—C8—H8120.8C23—C24—C25122.01 (15)
C8—C9—C10120.73 (16)C23—C24—H24119.0
C8—C9—H9119.6C25—C24—H24119.0
C10—C9—H9119.6C26—C25—C24118.99 (15)
C11—C10—C9120.73 (17)C26—C25—H25120.5
C11—C10—H10119.6C24—C25—H25120.5
C9—C10—H10119.6C27—C26—O2115.68 (15)
C12—C11—C10118.97 (16)C27—C26—C25120.28 (15)
C12—C11—H11120.5O2—C26—C25124.04 (15)
C10—C11—H11120.5C26—C27—C28120.06 (16)
C11—C12—C7120.44 (15)C26—C27—H27120.0
C11—C12—C13128.72 (15)C28—C27—H27120.0
C7—C12—C13110.80 (14)C27—C28—C23120.85 (16)
C12—C13—C14113.50 (13)C27—C28—H28119.6
C12—C13—C1101.01 (12)C23—C28—H28119.6
C14—C13—C1109.36 (12)O2—C29—C30114.11 (14)
C12—C13—C23107.59 (12)O2—C29—H29A108.7
C14—C13—C23112.64 (12)C30—C29—H29A108.7
C1—C13—C23112.21 (13)O2—C29—H29B108.7
C15—C14—C19117.84 (14)C30—C29—H29B108.7
C15—C14—C13121.86 (14)H29A—C29—H29B107.6
C19—C14—C13120.16 (14)C31—C30—C29177.1 (2)
C14—C15—C16121.61 (15)C30—C31—H31179.6 (16)
C6—C1—C2—C3−0.3 (2)C12—C13—C14—C15−17.1 (2)
C13—C1—C2—C3−179.70 (15)C1—C13—C14—C1594.84 (17)
C1—C2—C3—C4−0.9 (2)C23—C13—C14—C15−139.66 (15)
C2—C3—C4—C50.8 (3)C12—C13—C14—C19167.42 (14)
C3—C4—C5—C60.5 (2)C1—C13—C14—C19−80.65 (17)
C4—C5—C6—C1−1.7 (2)C23—C13—C14—C1944.9 (2)
C4—C5—C6—C7177.91 (16)C19—C14—C15—C160.7 (2)
C2—C1—C6—C51.6 (2)C13—C14—C15—C16−174.94 (15)
C13—C1—C6—C5−178.88 (14)C14—C15—C16—C170.2 (3)
C2—C1—C6—C7−178.09 (14)C20—O1—C17—C1627.2 (2)
C13—C1—C6—C71.44 (17)C20—O1—C17—C18−153.71 (14)
C5—C6—C7—C80.7 (3)C15—C16—C17—O1177.96 (15)
C1—C6—C7—C8−179.64 (16)C15—C16—C17—C18−1.1 (2)
C5—C6—C7—C12−179.73 (16)O1—C17—C18—C19−178.06 (14)
C1—C6—C7—C12−0.10 (18)C16—C17—C18—C191.0 (2)
C12—C7—C8—C90.7 (2)C17—C18—C19—C14−0.2 (2)
C6—C7—C8—C9−179.79 (16)C15—C14—C19—C18−0.7 (2)
C7—C8—C9—C10−0.7 (3)C13—C14—C19—C18174.99 (14)
C8—C9—C10—C11−0.3 (3)C17—O1—C20—C21−178.77 (13)
C9—C10—C11—C121.4 (3)C12—C13—C23—C2486.88 (17)
C10—C11—C12—C7−1.4 (2)C14—C13—C23—C24−147.28 (15)
C10—C11—C12—C13−178.96 (15)C1—C13—C23—C24−23.34 (19)
C8—C7—C12—C110.3 (2)C12—C13—C23—C28−86.21 (17)
C6—C7—C12—C11−179.24 (14)C14—C13—C23—C2839.6 (2)
C8—C7—C12—C13178.31 (14)C1—C13—C23—C28163.57 (15)
C6—C7—C12—C13−1.28 (18)C28—C23—C24—C251.5 (2)
C11—C12—C13—C14−63.3 (2)C13—C23—C24—C25−171.88 (15)
C7—C12—C13—C14118.92 (15)C23—C24—C25—C26−0.3 (2)
C11—C12—C13—C1179.74 (16)C29—O2—C26—C27178.32 (14)
C7—C12—C13—C11.99 (16)C29—O2—C26—C25−2.0 (2)
C11—C12—C13—C2362.0 (2)C24—C25—C26—C27−1.6 (2)
C7—C12—C13—C23−115.75 (15)C24—C25—C26—O2178.69 (15)
C2—C1—C13—C12177.43 (15)O2—C26—C27—C28−178.08 (15)
C6—C1—C13—C12−2.06 (16)C25—C26—C27—C282.2 (3)
C2—C1—C13—C1457.5 (2)C26—C27—C28—C23−0.9 (3)
C6—C1—C13—C14−121.99 (14)C24—C23—C28—C27−0.9 (2)
C2—C1—C13—C23−68.3 (2)C13—C23—C28—C27172.36 (15)
C6—C1—C13—C23112.26 (14)C26—O2—C29—C30−64.78 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C29—H29A···O1i0.992.463.358 (2)151
Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC31H22O2
Mr426.49
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)11.0047 (8), 12.9686 (9), 15.4371 (11)
V (Å3)2203.1 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		21245, 2861, 2658
Rint0.042
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.082, 1.04
No. of reflections2861
No. of parameters306
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.18, −0.20
Absolute structure2204 Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C29—H29A···O1i0.992.463.358 (2)151
Symmetry code: (i) −x+2, y+1/2, −z+3/2.
 

Acknowledgements

The authors thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2009). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHamciuc, C., Hamciuc, E., Ipate, A. M., Cristea, M. & Okrasa, L. (2009). J. Appl. Polym. Sci. 113, 383–391.  Web of Science CrossRef CAS Google Scholar
 First citationShah, K., Yousuf, S., Raza Shah, M. & Ng, S. W. (2010). Acta Cryst. E66, o1705.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1939
https://doi.org/10.1107/S1600536810025833
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